Oxidizable Ketones: Persistent Radical Cations from the Single-Electron Oxidation of 2,3-Diaminocyclopropenones.
O-centered radicals
cyclopropenium
ligand dissociation
oxidation
radical cations
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
11 Jun 2019
11 Jun 2019
Historique:
received:
20
02
2019
revised:
29
03
2019
pubmed:
10
4
2019
medline:
10
4
2019
entrez:
10
4
2019
Statut:
ppublish
Résumé
Single electron oxidation of 2,3-diaminocyclopropenones is shown to give rise to stable diaminocyclopropenium oxyl (DACO) radical cations. Cyclic voltammetry reveals reversible oxidations in the range of +0.70-1.10 V (vs. SCE). Computational, EPR, and X-ray analysis support the view that the oxidized species is best described as a cyclopropenium ion with spin density located on the heteroatom substituents, including 23.5 % on oxygen. The metal-ligand behavior of the DACO radical is also described.
Identifiants
pubmed: 30964215
doi: 10.1002/anie.201902265
pmc: PMC6546530
mid: NIHMS1029597
doi:
Types de publication
Journal Article
Langues
eng
Pagination
8049-8052Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM127135
Pays : United States
Organisme : National Institute of General Medical Sciences
ID : GM127135
Organisme : National Institute of General Medical Sciences
ID : GM102611
Organisme : National Science Foundation
ID : DGE-16-44869
Organisme : NIGMS NIH HHS
ID : R01 GM102611
Pays : United States
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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